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Regional Director of Retail

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Confidential Jobs
Full Time position
Listed on 2026-03-05
Job specializations:
  • Retail
    Retail & Store Manager
  • Management
    Retail & Store Manager, Operations Manager
Salary/Wage Range or Industry Benchmark: 100000 - 125000 USD Yearly USD 100000.00 125000.00 YEAR
Job Description & How to Apply Below

A well established, multi state cannabis retailer is seeking a Director of Retail Operations to lead dispensary performance across an assigned region. This leader will be responsible for driving strong store execution, developing high performing teams, and ensuring a consistent, compliant, and customer first experience across all locations.

This role is ideal for a hands on retail operator who thrives in a fast paced, regulated environment and knows how to balance culture, compliance, and commercial performance.

What You’ll Own
  • Regional Retail Leadership
  • You will oversee multiple dispensary locations, partnering closely with General Managers to ensure day to day execution, strong sales performance, and operational consistency.
  • Performance & Growth
  • You will be accountable for sales, profitability, inventory accuracy, and bonus target achievement while identifying opportunities to improve efficiency and customer experience.
  • Store Operations & Compliance
  • You will set clear operational expectations across dispensaries, continuously improving processes, protocols, and workflows while ensuring all regulatory requirements are met.
  • People & Culture
  • You will build strong relationships with store leadership, reinforce a safe and inclusive culture, reduce turnover, and support talent development and succession planning.
  • Customer & Community Experience
  • You will leverage customer feedback and community insights to elevate service standards and drive loyalty across the region.
  • Cross Functional Partnership
  • You will collaborate with corporate retail leadership, HR, and Talent Acquisition to execute staffing plans, roll out initiatives, and align retail operations with broader company strategy.
  • Reporting & Insights
  • You will provide regular updates on inventory, sales trends, and store performance, using data to inform decisions and prioritize improvements.
What You Bring
  • Multi unit retail leadership experience, ideally in cannabis, hospitality, or highly regulated retail
  • At least seven years of experience leading store or district level teams
  • Proven ability to coach General Managers and build high performing teams
  • Strong operational discipline with a customer centric mindset
  • Comfort interpreting financial reports and using performance data to drive results
  • Excellent communication and stakeholder management skills
  • Ability to handle confidential information with discretion
  • Passion for the cannabis industry and serving the adult use and medical cannabis community
  • High school diploma or GED required;
    Bachelor’s degree preferred
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